The Gentleman’s Guide to Tokyo

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David Coggins, a lifelong student and collector of mid-century Americana, makes a pilgrimage to Tokyo and discovers a city where the old-fashioned martini and RFK-era suit are not just being revived but remastered.

Kohei Take

At Caid Modern Tailoring, the handmade suits are updates of classic American cuts.

Anyone who's ever worn a pair of jeans knows that Levi Strauss may have invented jeans but the Japanese perfected them. Where would we be, really, without their 1990s-era embrace of selvedge denim?

But the truth is that the Japanese’s fascination with mid-century Americana goes far beyond jeans. This fixation is, depending on how you look at it, either perfectly understandable or just a little perverse: America, after all, occupied Japan from 1945 to 1952, following the country’s defeat in World War II. It was a disorienting period of recalibration for the Japanese, who lost not only the war but, for a period, their sense of self—something they wouldn’t recover until the 1960s, when the country underwent its startling transformation to modernity (and then, in the ’80s, hyper-modernity).

What’s inarguable, however, is that the Japanese have always been obsessives . . . and what’s more, once they become obsessed with something, they invariably improve upon it: a lesson that style writer and professional bon vivant David Coggins learned decades ago, as a freshly minted college graduate, on his first of many visits to Japan. “I’ve always collected classic men’s clothes,” says Coggins, who’s a creative consultant for Freemans, the New York City–based fantasyland of men’s style. “I actually bought shoes—without even knowing if they’d fit—from Douglas Fairbanks, Jr.’s estate auction.” But in Tokyo, Coggins discovered people whose dedication to American nostalgia eclipsed even his own—be they vintage-store owners selling beautifully preserved World War II Army jackets or tailors dedicating themselves to re-creating the perfect RFK-era sack suit. And so we asked him to share with us his favorite time-travel destinations in Tokyo: places where even the most die-hard nostalgist would find himself wondering if he hadn’t, somehow, traveled back in time.

Kohei Take

Left: Shirt collars at Caid Modern Tailoring. Right: Whiskey on the rocks at the Orchid Bar.

Orchid Bar

When the Okura Hotel opened on the edge of Roppongi in 1962, it was a modernist sensation: Designed by architect Yoshiro Taniguchi, it quickly became a symbol of the country’s leap into the postwar decades of rapid wealth and globalization. Today, the Okura is a luxury hotel, but despite the changes visited on both the hotel and the city, its iconic Orchid Bar remains untouched. With its low ceilings, wood accents, and discreet stained glass panels, the Orchid—which has just 15 bar seats—still recalls a more civilized age of travel. But aside from the soothing atmosphere, the real reason to come here is the whiskey. The entry to the bar takes you past a series of 20-odd glass lockers stocked with longtime customers’ extraordinary collections (I saw a bottle of 1971 Macallan, which might fetch $10,000—if you can find one for sale), and once seated, you can order whiskey of varying ages: a 17-year-old Hibiki, one of Japan’s finest, is about $20. If you take it on the rocks, your drink will be poured over a perfectly round orb of ice the size of an orange (2-10-4 Toranomon, Minato-ku; hotelokura.co.jp).

Sushi Nakamura

The unassuming, Michelin-starred Sushi Nakamura is behind an understated sliding door in the bar-crowded Roppongi district. Outside, the streets are lively and noisy, but inside this dim, hushed space—its gorgeous cypress bar seats just 11—you feel miles away. It’s the ideal setting for sushi that suggests chamber music of the highest order: intimate, honest, and direct. The menu here is omakase, and along with a carefully paced selection of 12 or so pieces of sushi or sashimi—clam, lightly brushed with soy-lemon dressing and a sprinkle of sea salt, served on a mound of warm rice; rich, savory mackerel—you’ll be treated to a few cooked dishes, including, perhaps, braised bonito. Both the gracious staff—led by the restrained head chef, Masanori Nakamura—and the elegant, all-Japanese crowd contribute to a dining experience that feels both singular and timeless (7-17-16 Roppongi, Minato-ku; 81-3-3746-0856; entrées from $165).

Franklin Tailored

Since the 1960s, Tokyoites have had a highly cultivated taste for traditional American Ivy League dress; indeed, you’ll see examples of this around Tokyo, where men of all ages favor seersucker, herringbone, or pinstripes. “The Japanese well understand that Ivy style is a classic look which has stood the test of time,” says Patricia Mears, deputy director of the Museum at FIT in New York and curator of the 2012 FIT exhibition “Ivy Style.” Now, however, the Japanese aren’t just tracking down original tweed jackets and Levi’s—they’re making their own masterpieces. At Franklin Tailored, every American-inspired piece of clothing—from the suits in indigo Japanese denim to the jeans and Western-inspired shirts—is made just north of Tokyo, and often of luxurious locally sourced fabrics, like soft madras and hand-dyed indigo wool. The small shop is on the second floor of a building in the Kanda district, just outside the city center, and with its wooden cabinets and retro fixtures feels like an airy version of a Yale dorm room from the 1950s. Along with suits and trousers, young designer Shuji Itai makes what might be the world’s best oxford shirt. Lightweight Japanese cotton, slim, and with a soft collar that looks perfect with or without a tie, it feels like it’s already your favorite shirt as soon as you try it on (3-3-2 Iwamoto-cho, Chiyoda-ku; 81-3-5809-1888; the-ft.com).

Kohei Take

Preppy style at Franklin Tailored.

Caid Modern Tailoring

With its walls hung with black-and-white photos of American style icons (Humphrey Bogart, Jack Lemmon), stacks of 1950s Esquires and GQs, and a vintage turntable playing Ella Fitzgerald, Caid Modern Tailoring—on the second floor of a modern building in bustling, neon-lit Shibuya—feels very much like a platonic ideal of a Senator Kennedy–era Brooks Brothers store. It’s all the vision of owner Yuhei Yamamoto, a gracious and immaculately dressed tailor in his forties who has made it his mission to keep alive the century-old Brooks Brothers sack suit (albeit with some tweaks: Yamamoto’s waists are slightly more defined than the original’s). A suit here costs between $1,950 and $2,950 and takes about a month to make, from initial measurements to pickup. But even if you don’t have that kind of time, you won’t be able to stop yourself from marveling at Yamamoto’s fabrics, from the discontinued bolts of robust textured wool from venerable mills like England’s Taylor & Lodge to the exact brown herringbone tweed of Steve McQueen’s coat in the 1968 movie Bullitt. There’s also a selection of smart accessories, including silver cufflinks, silk pocket squares, tweed hunting caps, and, best of all, handmade rep ties in a variety of classic colors, which sell for about $100 (42-15 Udagawa-cho Nakajima Bldg.; Shibuya-ku; 81-3-6685-1101; tailorcaid.com).